Certificate of payment for J. Bird and the enlisted help of John Patterson Osterhout, an attorney, in collecting the debt. On the back of the certificate it states that the debt was paid in full on March 15, 1855. Included is a business card for John Patterson Osterhout. The card states he is an attorney for Bellville, Texas and on the back of the card is an agreement for another collection to be done by John.

Letter from Chaplin F. Phillips to John Patterson Osterhout discussing his family. Chaplin was glad to find another one of his father's friends and told John that he would like to speak with him. He told John that if he was ever in Chicago he should come visit.

Letter from Gertrude Osterhout to her sisters, Ora and Junia Roberts Osterhout. She wrote to update her sisters about her life at school. She included small bits of news regarding her studies and plans to go on a picnic. She asked about the family orchards and requested that her sisters send her a box of the fruit.

Letter from Leyman Richardson to his friend, John Patterson Osterhout, in response to a letter John sent a month earlier. Leyman was grateful to hear that John had survived the Civil War and informed him of what was happening with the Richardson family. The government requested that Leyman be in charge of a school for children who were orphaned by the war, but decided it was too big of a project for his family. Included is an envelope addressed to "John P. Osterhout."

Letter from Ora Osterhout to her brother, Paul Osterhout, with news from home. She expressed concern over her brother's profession as a doctor since recently, a doctor in Belton was blamed for the death of a patient. Among other local gossip, Ora mentioned that their brother, Jeremiah, and his wife did not allow each other to leave without the other as they were jealous of them talking to members of the opposite sex.